2-Ethylbutyric acid → 16beta-Ethyl-17beta-(2-ethylbutyryl)oxyacetoxy-4-estren-3-one

HRID 64712

Reaction equation

HRID 64712 reaction equation
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24]Br)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].[CH2:27]([CH:29]([CH2:33][CH3:34])[C:30]([OH:32])=[O:31])[CH3:28]>CC(C)=O.[OH-].[Na+]>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][O:32][C:30](=[O:31])[CH:29]([CH2:33][CH3:34])[CH2:27][CH3:28])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Participants

5

Reactant 2

HCID 69152-Ethylbutyric acidHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046696716beta-Ethyl-17beta-(2-ethylbutyryl)oxyacetoxy-4-estren-3-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 35 ml of acetone is dissolved 1.0 ml of 2-ethylbutyric acid, and 4.6 ml of 2N-NaOH and then 1.9 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are added to the above solution. The mixture is refluxed for 3 hours. The acetone is distilled off under reduced pressure and the residue is extracted with two 100 ml portions of ethyl acetate. The organic layers are combined, washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 50 ml of ether, elution is carried out with 300 ml of the same solvent. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.63 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. distillationThe acetone is distilled off under reduced pressure
  3. extractionthe residue is extracted with two 100 ml portions of ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure
  7. washpassage of 50 ml of ether, elution
  8. customThe eluate is evaporated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-685484c6284b41cb99dbeb91de9c8807
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Linked notes

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